Acetone → 1,1-Dimethylethyl 2-chloro-3,3-dimethyl-2-oxiranecarboxylate

HRID 1657709Notes

Reaction equation

HRID 1657709 reaction equation
Cl[CH:2]([Cl:10])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:11][C:12]([CH3:14])=[O:13].O>O1CCCC1>[Cl:10][C:2]1([O:13][C:12]1([CH3:14])[CH3:11])[C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4]

Participants

5

Reactant 3

HCID 180AcetoneHCID 962WaterHCID 30164831,1-Dimethylethyl dichloroacetate

Product 1

HCID 145822571,1-Dimethylethyl 2-chloro-3,3-dimethyl-2-oxiranecarboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 70.8 g of potassium tert.-butylate in 500 ml of tetrahydrofuran was added over 30 minutes under an inert atmosphere to 111 g of tert.-butyl dichloroacetate and 35.5 g of acetone at 0°C and after letting the mixture return to room temperature, the mixture was stirred for 1 hour and poured into iced water. The mixture was extracted with petroleum ether and the extract was washed twice with water and dried over sodium sulfate. 40 g of alumina were added thereto and after stirring, the mixture was filtered to remove mineral products. The solvent was removed from the filtrate by distillation under reduced pressure to obtain 116.5 g of tert.-butyl 2-chloro-2,3-epoxy-3-methyl-butanoate in the form of a colorless liquid soluble in the usual organic solvents and insoluble in water.

Workup

  1. customto room temperature
  2. extractionThe mixture was extracted with petroleum ether
  3. washthe extract was washed twice with water
  4. dry with materialdried over sodium sulfate
  5. addition40 g of alumina were added
  6. stirringafter stirring
  7. filtrationthe mixture was filtered
  8. customto remove mineral products
  9. customThe solvent was removed from the filtrate by distillation under reduced pressure

Sources & evidence

ORD record
ord-9ed98c51d35542039254c853557a2d85
Source dataset
uspto-grants-1976_06
Patent number
US03962223

Reaction notes

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